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Report | Regular issue | Vol 23, No. 10, 1985, pp.2571-2575
Published online, 1st January, 1970
DOI: 10.3987/R-1985-10-2571
An Oxidative 1,3-Dithiolane → Dihydro-1,4-dithiin Rearrangement

Luis Angel Maldonado* and Norberto Manjarrez

*Div. Estudios de Posgrado, Facultad de Química, Universidad Nacinal Autónoma, Circuito Exterior, Ciudad Universitaria, Coyoacán 04510, Mexico


In hot DMSO, compound 1 is converted into 2 in excellent yield. This conversion involves a 1,3-dithiolane → dihydro-1,4-dithiin rearrangement to 3, followed by oxidation of the allylic CH2. Appropriate experiments established the mechanism of this rearrangement-oxidation sequence.